CA2726005A1 - Process for the preparation of halogenated benzoic acid derivatives - Google Patents

Process for the preparation of halogenated benzoic acid derivatives Download PDF

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Publication number
CA2726005A1
CA2726005A1 CA2726005A CA2726005A CA2726005A1 CA 2726005 A1 CA2726005 A1 CA 2726005A1 CA 2726005 A CA2726005 A CA 2726005A CA 2726005 A CA2726005 A CA 2726005A CA 2726005 A1 CA2726005 A1 CA 2726005A1
Authority
CA
Canada
Prior art keywords
preparation
benzoic acid
acid derivatives
halogenated benzoic
fluoro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA2726005A
Other languages
French (fr)
Other versions
CA2726005C (en
Inventor
Stephan Bachmann
Stefan Hildbrand
James Jappy
Dinesh Maganbhai Patel
Christophe Pfleger
Robert John Ernest Tidswell
Rene Trussardi
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of CA2726005A1 publication Critical patent/CA2726005A1/en
Application granted granted Critical
Publication of CA2726005C publication Critical patent/CA2726005C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/518—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of sulfur-containing compounds to >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/15—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/29—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with halogen-containing compounds which may be formed in situ

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The present invention comprises a process for the preparation of 3-chloro-2-fluoro-5- trifluoromethyl benzoic acid of the formula or of a salt thereof. 3-Chloro-2-fluoro-5-trifluoromethyl benzoic acid or salts thereof are versatile intermediates for the preparation of active pharmaceutical or agrochemical agents.

Claims
CA2726005A 2008-06-06 2009-05-28 Process for the preparation of halogenated benzoic acid derivatives Expired - Fee Related CA2726005C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08157757 2008-06-06
EP08157757.9 2008-06-06
PCT/EP2009/056560 WO2009147068A1 (en) 2008-06-06 2009-05-28 Process for the preparation of halogenated benzoic acid derivatives

Publications (2)

Publication Number Publication Date
CA2726005A1 true CA2726005A1 (en) 2009-12-10
CA2726005C CA2726005C (en) 2016-06-28

Family

ID=41056832

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2726005A Expired - Fee Related CA2726005C (en) 2008-06-06 2009-05-28 Process for the preparation of halogenated benzoic acid derivatives

Country Status (7)

Country Link
US (3) US20090306423A1 (en)
EP (1) EP2310349B1 (en)
JP (1) JP5529857B2 (en)
CN (1) CN102056883B (en)
CA (1) CA2726005C (en)
ES (1) ES2412755T3 (en)
WO (1) WO2009147068A1 (en)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2310349B1 (en) * 2008-06-06 2013-04-24 F. Hoffmann-La Roche AG Process for the preparation of halogenated benzoic acid derivatives
US20110313196A1 (en) 2010-06-18 2011-12-22 Stephan Bachmann Novel process
CN102617339A (en) * 2012-03-05 2012-08-01 山西仟源制药股份有限公司 3-cyclopropylmethoxy-4-halogen benzoic acid or derivative and application thereof
CN103012122B (en) * 2012-12-10 2014-01-08 天长市天佳化工科技有限公司 Preparation method of 2-chloro-5-(trifluoromethyl) benzoic acid
JP7018327B2 (en) * 2018-02-05 2022-02-10 日本曹達株式会社 Method for producing benzaldehyde derivative
CN110156637A (en) * 2019-06-18 2019-08-23 宁波美诺华药业股份有限公司 A kind of preparation method of the chloro- 3- cyano -5- fluobenzoic acid of 2,4- bis-
CN110627714A (en) * 2019-10-16 2019-12-31 安庆博曼生物技术有限公司 Synthetic method of 3-fluoro-2-trifluoromethyl isonicotinic acid
CN112079703A (en) * 2020-09-01 2020-12-15 常州工学院 Preparation method of 2-chloro-4-fluoro-benzaldehyde
CN112679374A (en) * 2021-01-12 2021-04-20 湖南复瑞生物医药技术有限责任公司 Preparation method of 2-fluoro-6- (trifluoromethyl) benzamide
CN113999106A (en) * 2021-11-26 2022-02-01 八叶草健康产业研究院(厦门)有限公司 Preparation method of 4-bromo-2, 5-dichlorobenzoic acid
CN114436810A (en) * 2021-12-23 2022-05-06 宁夏忠同生物科技有限公司 Method for preparing o-trifluoromethylbenzoic acid
CN115959979A (en) * 2022-12-29 2023-04-14 南京正荣医药化学有限公司 Preparation method of 3-chloro-4-fluoro-5-trifluoromethyl trifluoroacetophenone

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3823134A (en) * 1969-10-08 1974-07-09 Sandoz Ag Dichloro-alpha,alpha,alpha-trifluorotoluamides
US4469893A (en) * 1982-03-22 1984-09-04 Occidental Chemical Corporation Method for the preparation of nitrodiphenyl ethers
US5196593A (en) * 1988-10-31 1993-03-23 Occidental Chemical Corporation Halogenated trifluoromethylbenzenes
IT1243410B (en) 1990-12-17 1994-06-10 Donegani Guido Ist PROCEDURE FOR THE FUNCTIONALIZATION OF TRIFLUOROMETILBENZENI
DE4301245A1 (en) 1993-01-19 1994-07-21 Bayer Ag Fluorotrifluoromethylbenzoic acid derivatives
FR2743066B1 (en) 1995-12-28 1998-03-27 Rhone Poulenc Chimie PROCESS FOR THE SYNTHESIS OF AN ARTHATIC DERIVATIVE ORTHODISUBSTITUTED BY A HALOGEN ATOM OTHER THAN FLUORINE AND BY A CYANO GROUP
EP0881207A4 (en) 1996-07-30 1999-11-24 Nippon Soda Co 2,3-dihalogeno-6-trifluoromethylbenzene derivatives and processes for the preparation thereof
US6348624B1 (en) 1998-01-09 2002-02-19 The Procter & Gamble Co. Process for making certain benzoic acid compounds
US6355843B1 (en) 1998-05-05 2002-03-12 Eli Lilly And Company Purification of carboxaldehyde
US6677479B2 (en) 2001-11-13 2004-01-13 Clariant Finance Lbvi Limited Substituted fluoroaromatics, process for preparing them and their use
EP2310349B1 (en) * 2008-06-06 2013-04-24 F. Hoffmann-La Roche AG Process for the preparation of halogenated benzoic acid derivatives

Also Published As

Publication number Publication date
US20120330055A1 (en) 2012-12-27
US20120130121A1 (en) 2012-05-24
JP2011521994A (en) 2011-07-28
ES2412755T3 (en) 2013-07-12
EP2310349A1 (en) 2011-04-20
US8642802B2 (en) 2014-02-04
US8329939B2 (en) 2012-12-11
CN102056883A (en) 2011-05-11
CN102056883B (en) 2014-11-12
WO2009147068A1 (en) 2009-12-10
EP2310349B1 (en) 2013-04-24
US20090306423A1 (en) 2009-12-10
JP5529857B2 (en) 2014-06-25
CA2726005C (en) 2016-06-28

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Legal Events

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EEER Examination request

Effective date: 20140515

MKLA Lapsed

Effective date: 20190528